Sulfinimines (THIOOXIMINE S-OXIDES): Asymmetric synthesis of methyl (R)-(+)-ȕ-Phenylalanate from (S)(+)-N-(BENZYLIDENE)-p-Toluenesulfinamide : Benzenepropanoic acid, ȕ-amino-, (R)-, methyl ester from Benzenesulfinamide, 4-methyl-N-(phenylmethylene)- [S-(E)]

Organic Syntheses

Volumn 77, Issue , 2000, Pages 50-

  Fanelli, Dean L ^b   Szewczyk, Joanna M ^b   Zhang, Yulian ^b   Venkat Reddy, G ^b   Burns, David M ^b   Davis, Franklin A ^a   Unch, James ^b   Hart, David J ^b  

^a Temple University   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85027886124     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.077.0050     Document Type: Article

References (49)

1. Procedure adapted from Davis, F. A.; Zhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D. L.; Zhang, H. J. Org. Chem. 1999, 64, 1403
2. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Thimma Reddy, R.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
3. Procedure adapted from Davis, F. A., Reddy, R. E.; Szewczyk, J. M. J. Org. Chem. 1995, 60,7037.
4. Solladie, G. Synthesis 1981, 185.
5. For reviews of the chemistry of sulfinimines see: Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13;
6. Davis, F. A.; Reddy, R. E. "Synthesis of Nonracemic ȕ-Amino Acids via Chiral Sulfinimines," Enantioselective Synthesis of ȕ-Amino Acids, E. Juaristi, Ed., Wiley-VCH: NY, 1997, Chapter 6, p 127.
7. Annunziata, R.; Cinquini, M.; Cozzi, F. J. Chem. Soc., Perkin Trans. 1 1982, 339
8. Davis, F. A.; Reddy, T. R.; Reddy, R. E. J. Org. Chem. 1992, 57, 6387.
9. Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913.
10. Juaristi, E., Ed. "Enantioselective Synthesis of Ε-Amino Acids"; Wiley-VCH: New York, 1997.
11. Davis, F. A.; Reddy, R. E. Tetrahedron: Asymmetry 1994, 5, 955.
12. Jiang, J.; Schumacher, K. K.; Joullié, M. M; Davis, F. A.; Reddy, R. E. Tetrahedron Lett. 1994, 35, 2121.
13. Davis, F. A.; Szewczyk, J. M.; Reddy, R. E., J. Org. Chem. 1996, 61, 2222.
14. (Amines): (a) Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268;
15. Hose, D. R. J.; Mahon, M. F.; Molloy, K. C.; Raynham, T.; Wills, M. J. Chem. Soc., Perkin Trans. I 1996, 691. See also ref. 15.
16. Moreau, P.; Essiz, M.; Merour, J-Y.; Bouzard, D. Tetrahedron: Asymmetry, 1997, 8, 591.
17. (Į-Amino acids): (a) Davis, F. A.; Srirajan, V.; Titus, D. J. Org. Chem. 1999, 64, 6931;
18. Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396;
19. Portonovo, P.; Liang, B.; Joullie, M. M. Tetrahedron: Asymmetry, 1999, 10, 1451;
20. Bravo, P.; Crucianelli, M.; Vergani, B.; Zanda, M. Tetrahedron Lett. 1998, 39, 7771;
21. Hua, D. H.; Lagneau, N.; Wang, H.; Chen, J. Tetrahedron: Asymmetry 1995, 6 , 349. See also refs. 21,22.
22. Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y-H. J. Org. Chem. 1996, 61, 440.
23. Davis, F. A.; Fanelli, D. L. J. Org. Chem. 1998, 63, 1981.
24. (ȕ-Amino acids): (a) Wei, H-X.; Hook, J. D.; Fitzgerald, K. A.; Li, G. Tetrahedron: Asymmetry, 1999, 10, 661;
25. Li, G.; Wei, H-X.; Whittlesey, B. R.; Batrice, N. N. J. Org. Chem. 1999, 64, 1061;
26. Li, G.; Wei, H-X.; Hook, J. D. Tetrahedron Lett. 1999, 40, 4611;
27. Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12;
28. Davis, F. A.; Szewczyk, J. M. Tetrahedron Lett. 1998, 39, 5951;
29. Garcia Ruano, J. L.; Fernandez, I.; del Prado Catalina, M.; Hermoso, J. A.; Sanz-Aparicio, J.; Martinez-Ripoll, M. J. Org. Chem. 1998, 63, 7157;
30. Adamczyk, M.; Reddy, R. E. Tetrahedron: Asymmetry, 1998, 9, 3919;
31. Fujisawa, T.; Kooriyama, Y.; Shimizu, M. Tetrahedron Lett. 1996, 37, 3881;
32. Hua, D. H.; Miao, S. W.; Chen, J. S.; Iguchi, S. J. Org. Chem. 1991, 56, 4.
33. (Aziridines/2H-Azirines): (a) Ruano, J. L. G.; Fernandez, I.; Catalina, M. Cruz, A. A. Tetrahedron: Asymmetry, 1996, 7, 3407;
34. Davis, F. A.; Reddy, G. V.; Liu, H. J. Am. Chem. Soc. 1995, 117, 3651. See also refs. 34,35,36,37,38,39
35. Davis, F. A.; Zhou, P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243.
36. Davis, F. A.; Liu, H.; Reddy, G. V. Tetrahedron Lett. 1996, 37, 5473.
37. Davis, F. A.; Zhou, P. Tetrahedron Lett. 1994, 35, 7525.
38. Davis, F. A.; Reddy, G. V. Tetrahedron Lett. 1996, 37 , 4349.
39. Davis, F. A.; Reddy, G. V.; Liang, C.-H. Tetrahedron Lett. 1997, 38, 5139.
40. Davis, F. A.; Liang, C.-H.; Liu, H. J. Org. Chem. 1997, 62, 3796.
41. (Alkaloids): Balasubramanian, T.; Hassner, A. Tetrahedron: Asymmetry, 1998, 9, 2201.
42. Balasubramanian, T.; Hassner, A. Tetrahedron Lett. 1996, 37, 5755.
43. Viso, A.; de la Pradilla, R. F.; Guerrero-Strachan, C.; Alonso, M.; Martinez-Ripoll, M.; Andre, I. J. Org. Chem. 1997, 62, 2316.
44. Davis, F. A.; Andemichael, Y. W. J. Org. Chem. 1999, 64, 0000;
45. Davis, F. A.; Andemichael, Y. W., Tetrahedron Lett. 1998, 39, 3099.
46. (Aziridine 2-phosphonates/Azirinyl phosphonates): Davis, F. A.; McCoull, W. Tetrahedron Lett. 1999, 40, 249.
47. Mikolajczyk, M.; Lyzwa, P.; Drabowicz, J.; Wieczorek, M. W.; Blaszczyk, J. J. Chem. Soc., Chem. Commun. 1996, 1503.
48. Mikolajczyk, M.; Lyzwa, P.; Drabowicz, J. Tetrahedron: Asymmetry, 1997, 8, 3991.
49. Lefebvre, I. M.; Evans, S. A., Jr. J. Org. Chem. 1997, 62, 7532.